Silver halide solvent containing developers and process



United States Patent New Jersey No Drawing. Filed Oct. 23, 1961, Ser.No. 147,055

20 Claims. (Cl. 9661) This invention relates to photography, and moreparticularly, to photographic developers for use in reversal processingof photographic color films and papers.

In multi-layer photographic elements used for color photography, thereare usually at least three selectively sensitive emulsion layers coatedon a conventional photographic support, such as cellulose ester film,paper, polyvinyl resin film, polyester film, etc. For example, theuppermost silver halide emulsion layer may be bluesensitive, while thesilver halide emulsion layer closest to the support may bered-sensitized. Between these two emulsion layers, there may be a greensensitized silver halide emulsion layer. Frequently, a yellow filterlayer is used between the blue-sensitive and the green-sensitized silverhalide emulsion layer. Of course, additional silver halide emulsionlayers, gelatin interlayers, and the like, may also be present. Thesilver halide emulsion layers may contain some of the processingingredients, such as the color-forming compounds or couplers. Inprocessing multi-layer color materials of the type useful in ourinvention, the photographic material is first processed to aconventional black-and-white silver negative in a developer which doesnot contain a developing agent capable of coupling with any of thecolor-forming compounds or couplers which may be present. Withoutremoving unexposed silver halide, the material is given a reversalreexposure, followed by color development. The technique of colorreversal processing is well known to those skilled in the photographicart and color materials which can be used in such processing have beenpreviously described in a number of domestic and foreign patents, suchas Mannes et al. US. Patent 2,252,718, issued August 19, 1941.

The color materials useful in the present invention include those havingsilver halide emulsion layers containing the color-forming materials orcouplers in a layer, or layers, as well as color materials intended forprocessing in a color developer which contains the color coupler.

3,128,182 Patented Apr. 7, 1964 them have the added disadvantage ofreducing the defini- It is, therefore, an object of our invention toprovide improved developers for reversal color photography. Anotherobject is to provide a method of processing reversal color materialsusing the improved developers of our invention. Other objects willbecome apparent from a consideration of the following description andexamples. In the processing of various photographic materials, it hasbeen rather common to employ silver halide solvents in the photographicsilver halide developing compositions for the purpose of acceleratingeither black-andwhite or color development. However, some of the amineswhich have been previously used in the developing compositions ofphotographic color materials have been found to be highly toxic andquite volatile. In addition, some of these amines readily formcarbamates in the photographic developers commonly used and some of tionof the colored images formed in certain of the sensitized layers,particularly the green-sensitized layer which develops into a magentaimage. Some of these amines also interfere with development so thatdevelopment does not proceed to the production of an image of desireddensity.

While some amines have useful properties for specific types ofphotographic developers, such properties are usually unique and limitedto the use of a particular set of conditions. These amine silver halidesolvents when used in the black-and-white developers will affect thecurve shapes of all sensitized layers as well as affecting the overallspeed and fog, while in a color developer, the curve shape of the layerbeing developed is primarily affected, as well as the covering power ofthe resulting dye, silver/dye ratio, and the sharpness of the dye image.The activity of certain of the silver halide solvents, such asisopropylamine, particularly in the black-and-whitedeveloper, is lowerwhere the alkaline material is an alkali metal carbonate, since suchsilver halide solvents readily form carbamates with the carbonate,resulting in a serious loss of the silver halide solvent.

We have now found that the afore-mentioned difficulties in theblack-and-white developing solutions, as well as the color developingsolutions, can be entirely or large ly overcome by using as silverhalide solvents, cyclohexane compounds containing an amino radical, andin addition to the amino radical, a polar substituent, such as hydroxyl,amino, hydroxyalkyl (hydroxyethyl, hydroxypropyl, etc.), etc.Particularly useful cyclohexane compounds are those which contain anaminomethyl substituent. Typical cyclohexane compounds useful in ourinvention comprise 1,4-bis(methylamino)cyclohexane, 4-aminocyclohexanol, 1-cyclohexaneamino-Z-propanol, etc.

It has been found that the cyclohexane compounds of our invention, whenused either in the black-and-white negative developer, or in one or moreof the color developers, have adequate photographic activity and permitreasonable film speeds with very low fog density. They have lowvolatility, low toxicity, high water solubility and only a slighttendency to form carbamates under the alkaline conditions present inmany of these photographic developers. In addition, when thesecyclohexane compounds are employed in color developers, they show notendency to reduce the sharpness of the color images.

The cyclohexane compounds used as silver halide solvents in ourinvention can be employed under rather wide concentration ranges,depending upon the type of silver halide developer, concentration ofalkali, type of alkali, type of coupler, etc. In general, we have foundthat quite useful results are obtained in black-and-white silver halidenegative developers if the concentration of the cyclohexane compoundvaries from about 0.5 to 10 grams per liter. Approximately the sameconcentration ranges for the cyclohexane compound can be employed incolor developers, although we have found that especially good resultsare obtained within the range of about 1 to 8 grams per liter.

The cyclohexane compounds of our invention can be employed in a varietyof aqueous alkaline solutions containing various photographic developingagents. The black-and-white negative developing agents which have beenfound particularly useful in our invention comprise thedihydroxybenzenes, such as hydroquinone, toluquinone, etc.,N-methyl-p-aminophenol salts, etc., or mixtures of such developingagents. Also, useful in the negative developers of our invention are the3-pyrazolidones, such as 1-phenyl-3-pyrazolidone, 4,4-dimethyl-1-phenyl-3-pyrazolidone, etc.

Any of the conventional color-forming developing agents which have beenpreviously described in the prior art can be used in our invention. Thecolor-forming developers or developing agents which have been found tobe especially useful in our invention include aromatic primary aminescontaining an amino (substituted or not) or iiydroxyl substituent.Phenylenediamines and substitut-d derivatives thereof containing aprimary amino gr p are especially useful in our invention. Typical ofr-forrning developers are the sulfonarnido substituted penylenediaminesdisclosed in Weissberger et al., US. Pa nt 2,548,574, issued April 10,195]; the substituted p-p enylenediamines disclosed in Weissberger etal., US. Patent 2,566,271, issued August 28, 1951, etc.

The pH of the developers useful in our process, including both the colordevelopers and the black-and-whitc negative developers, can varydepending upon the particularv photographic material which is to beprocessed in the developers. In the case of color developers, it hasbeen found that the cyclohexane compounds of our invention areoutstanding at relatively high pH values, i.e., where the pH is at least10.0 and as high as 11.5 to 12.5.

Our invention is primarily directed to the development of the ordinarilyemployed gelatino-silver-balide developing-out emulsions, e.g.,gelatino-silver-chloride, -chlorobromide, -chioroiodide,-chiorobromiodide, -bromide, -bromiodide, etc. While the resultsillustrated below were obtained using gelatino-silver bromiodideemulsions, excellent results can be obtained using other silver halideemulsions. These emulsions can be coated in the usual manner on asuitable support, e.g.. glass, cellulose nitrate film, cellulose acetatefilm, polyvinyl film, polyester film, paper, metal, etc.

Photographic silver halide emulsions useful in our iuverition can alsocontain such addenda as chemical sensitizers, e.g.. sulfur sensitizers(e.g., allyl thiocarbarnide, thiourea. allyl isothiocyanate, cystine,etc), various gold compounds (eg. potassium chloroaurate, aurictrichloride, etc.) (see US. Patents 2,540,085; 2,597,856 and 2,597,915),various azaindene compounds (such as those disclosed in US. Patent2,716,062), condensation prodcol nets of alkylene oxides, such as thoseshown in US. Patent 2,400,532, as well as the additives mentioned inJones et al.,'U.S. Patent 2,937,089.

ypical color-forming compounds or couplers which areuseful in colorphotography, according to our inventior t, include the following:

l COUPLERS PRODUCING CYAN IMAGES 5- (p-amylphenoxybenze nesulfonamino) l-naphthol 5- N-benzyl-N naphtha]enesulfonamino l -naphthol5-(n-benzyl-N-n-valerylamino)-1-naphthol S-caproy] amino- 1 -naphtholZ-chloro-S-(N-n -valcrylN-pisopropylbenzylamino) -1- naph thol2,4-dichloro-5- (p -n itrobenzoyl-fi-o-hydroxyethylamino) l-naphth ol12,4-Qdichloro-5-palmitylamino-Lnaphthol 2,2-dihydroxy-5 ,5ditvromostilbenc S-diphcnylethcrsniionamido-l-naphthol l-hyd roxyZtN-isoa m3- l-N-phenyl napb tha mide l.-hydroxy-2-( N-psec amylphenyl)naphthamide X-hydroxyl -a-naphtho vl-1,2,3,4-tetrahydroquinoline2-lauryl-4-chloro phenol l-naphthol-2-carboxyiicu-11aphthalidc1-naphthol-5-sul fo-cycloh exy l n mide 5 -phenoxyacetam ino-l-napintS-B-phenylpropionylamino-i; 'thol Monochlor-S-(N-y-phcnylpr :j g"-psec.-amylbenzoylamino) -1-naphthol 2-acetylamino-5-methylphenol2-benzoylamino-3,S-dimethylpb-s 6- {'y-{ 4- ['y- 2,4-di-tert. amy lputyramido1phenoxy} acetamido}-2,4-dichloro iylphenol l-hydroxy-Z- 5-2,4-di-t ert. amylpr' 1oxy)-n-butyl]naphthamide 2-ct(p-tert.amylphenoxy) n butyi' 'ii no-S-methylphenol nino-4-chloro-5-ntethylphenol Z-(tf-tert. amylphenoxy-p-bcnz yl no-4-chl0ro-5-methylphenol 2-(4--tert.amyl-3'-phenoxybenzoyl.- 5 -3,5-dimethyll'phenolphenol 2-(4-tert. amyl-3-phenoxybenzoylamino) -3-meth vl-lphenol2-(4-tert. amyl-3'-phenoxybenzoylamino)--6-1neihyl-1- phenol 2-(4"-tert.amyl-3 '-phenoxybenzoyl amino -3,6-diniethylphenol 2,6-di(4"-tert. amyl3-p'hcnoxybcnzoylaminc)-l-phcnol 2-a (4'-tert.amylphenoxy)butyrylamino-i phenol2-(o-acetarnido-fi-phenylcthyl)-l-hydroxynaphthamide 2(4-tert.amyl-3--phenoxybenzoylamino)QLS-dimethyll-phenol 2-[a-(4-tert.amylphenoxy)-nbutyrylammold-methyllphenol 2(4-tert.amyl-3'-phcnoxybenzoylamino)-4-chloro' iphenol 3-[ x-(4'-tert.amylphcnory)-n-lmtyrylamino]-6-chlorophenol 3-(4"-tert.amyl-3-phenoxybenzoylamino) phenol 3-la-(4'-tert.amylphenoxy)-n-butyrylumino}-5-chlorophenol 3-{a-(4-tert.amylphenoxy)--n-butyrylamino}-Zchlorophenol I 2-a-(4'-tert.an'iylphenoxybutyryiamino)-5-chlorophcnol 2-(4-tert.amyl-B'-phenoxybenzoyiamino)-3-chlorophenol S-benzenesulfonaminodmaphthol 2,4-dichloro-5-bcnzcnesnliimamino-lmapbthol2,4-dichloro-5- (p-tolucnesulfonaminohl -naphthoi 5-(l,2,3,4-tetrahydronaphthalencfi-sullaminn t-l-naphti'toi2,4-dichloro-5-(4'-br0modiphcnyl-4-sullonamino)--lnaphthol5-(quinolinc-S-sulfamino)-Lnaphthol Any of the acylaminophenol couplersdisclosed in Sal- NlIC o-dn-o-Qonn C II etc.

COUPLERS PRODUCING MAGENTA IMAGES l-p-sec.amylphenyl-3-n-amyl-5-pyrazolone 2-cyanoacetyl-5-(p-sec.amylbenzoylamino)coumarone Z-cyanoacetylcoumarone-S- (n-amyl-p-sec.amylsulfanilide) 2-cyanoacctylcoumarone-S- (N-n-amyl-p-tert.amylsulfanilide) Z-cyanoacetylcoumarone-S-sulfon-N-n-butylanilideZ-cyanoacetyl-S -benzoylamino-coumarone2-cyanoacetylcoumarone-S-sulfonclimethylamideZ-cyanoacetylcoumarone-5-sulfon-N-methylanilide 2-cyanoacetylnaphthalenesulfon-N-methylanilide 2-cyanoacctylcoumarone5-(N-y-phenylpropyl)-p-tert.

amylsulfonanilide 1-p-laurylphenyl-3-methyl-5-pyrazolonc1-B-naphthyl-B-amyl-S-pyrazolone l-p-nitrophenyl-3 -n-amyl-5-pyrazolone1-pphenoxyphenyl-3-n-amyl-5-pyrazolone 1- henyl-3 -namyl-5-pyrazolone1,4-phenylene bis-3-( l-phenyl-S-pyrazolone) 1 -phenyl-3-acctylamino-5-pyrazolone 1-phenyl-3 -propionylamino-5-pyrazolone 1-phenyl-3-n-valerylamino-5 -pyrazolone 1-phenyl-3-chloroacetylamino-S-pyrazolone1-phenyl-3 -d ichl oro acetylamino-S-pyrazolone 1-phenyl-3-benzoylamino-5-pyrazolone l-phcnyl-3- m-aminobenzoyl)amino-S-pyrazolone l-phenyl-S-(p-sec. amylbenzoylamino)-5-pyrazolonel-phenyl-3 -diamylbenzoylamino-S-pyrazolone l -phenyl-3B-naphthoylamino-S-pyrazolone 1-phcnyl-3-phenylcarbamylamino-S-pyrazolone 1-phenyl-3-palmitylamino-S-pyrazolone 1-ph enyl-3 -henzenesulfonylamino-S-pyrazolone1-(p-phenoxyphcnyl)-3-(p-tcrt. amyloxybenzoyl)amino- 5- pyrazolone 1-(2',4,6-tribromophenyl -3-benzamido-5-pyrazolone 1-(2,4,6'-trichlorophenyl '-3-benzamido-5-pyrazolonel-(2',4',6'-trichlorophenyl)-3-phenylacetamido-5-pyrazolone l-(2',4',6-tribromophenyl -3 -phenylacetamido-5-pyrazolone 1-2,4'-dichlorophenyl -3- 3 2"',4"'-di-tert. aylphenoxyacetamido)benzamido] -5-pyrazolone I l- (2,4',6'-trichlorophenyl -3- 3 (2",4"-di-tert. amylv phenoxyacetamido benzamido] -5pyrazolone 1-( 2,4',6-tribromophenyl -3- 3 2',4'-di-tert.amylphenoxyacetamido benzamido] -5-pyrazolone l-2',4',6'-trichl0rophenyl -3- B- (2"',4"'-di-tert. amylphenoxy-propionamido] -5-pyrazolone1-(2,4,6-tribromophenyl)-3-[p-(2"',4"'-di-tert. amy1 phenoxy)-propionamido] -5-pyrazolone amido]-5-pyrazolone 1-(2',4',6'trichlorophenyl.).-3-(4-nitroanilino)-5Ppyrazolone COUPLERS "PRODUCING.YELLOW IMAGES N-amyl-p-benzoylacetaminobenzenesulfonateN-(4-anisoylacetaminobenzenesulfonyl -N.-benzy1-mtoluidine N-(4-benzoylacetaminobenzenesulfonyl) -N-benzyl-mtoluidine 1N-(4-benzoylacetaminobenzenesulfonyl)-N-n-amyl-p-= toluidineN-(4-benzoylacetaminobenzenesulfonyl)-N-benzvlaniline w-(p-Benzoylbenzoyl acetanilide w-Benzoylacet-2,S-dichloroanilidew-Benzoyl-p-sec. amylacetanilideN,N'-di(w-benzoylacetyl)-p-phenylenediamineN,N'-di-(acetoacetamino)diphenyl Z-methoxyacetanilide a-{3- a-(2,4-di-tert.-amylphenoxy) acetam1do]benzoyl sions of our inventioninclude those described in Spenceand Carroll US. Patent 2,640,776,issued June 2, 1953;

Weissbergcr et al. US. Patent 2,407,210, issued September 3, 1946, andWeissberger et al. US. Patent 2,474,293, issued June 28, 1959..

The following examples will serve to illustrate the manner of practicingour invention.

Example 1 A portion 'ofa gelatino-silver-bromiodide emulsion which hadbeen sensitized with a sulfur compound and a gold salt asmentioned-above, was'coated on a cellulose acetate support and dried.-The. coating was then cut into ,several strips and one strip of each wasthen exposed for second to'a 500w att, 3000 K. light source on anEastman Type II sensitomcter. One of the exposed strips was thendeveloped for 3 minutes in adeveloper having the following composition;

Sodium hexametaphosphate g 0.4 Sodium 'sulfite (anhydrous) g' 40.0N-methyl-p-aminophenolsulfate y g 5.0 Hydroquinone g 2.0 Sodiumcarbonate (monohydrate') g 25.0 Potassium bromide g 1.0 Potassium iodide(0.l% solution) ccs 2 Water to make one liter. (pl-I was 10.1 at70 F.)

The strip was then washed for about 2 minutes in .Water and ;then givena reversal exposure for about 10 seconds (flash) with a No. 2 Photofloodset at a distance of about 60 inches. The strip was then developed forapproximately minutes in a developer having the following formula:

Sodium hexametaphosphate g 1.0 Sodium sulfite (anhydrous) g 30 Sodiumsulfate g 30 Sodi'um bromide g 0.5 Potassium iodide (0.1% solution) ccs5 1,4-bis aminomcth yl cyclohexane -g- 5 Coupler 1 g 0.85 Sodfumhydroxide g 3 Col r developer g 3 Hy oxylamine sulfate g 0.35 Wa r tomake 1 liter. (p at 80 F. was 12.40.) v

1 (2,4,6-trichlorophenyl) 3 [ll-(4 nitrophenoxy)- acct niido]5-pvrazolone.

2 amino-N,N-diethyl-3-methylaniliue hydrochloride. The, strip was thenwashed for about minutes in water andtreated for about 2 mintues in asilver bleach bath having the following composition:

, G. Potassium ferricyanide 100 Potassium bromide 10 Borax n 7.5 Boricacid 5.0 Water to make 1 liter.

The strip was then treated for about 2 minutes in a fixing bath havingthe following composition:

1 Ga Sodium thiosulfate (pentahydrate) 200 Sodium sulfite (anhydrous) 10Water to make 1 liter.

Thei strip was then washed in water and dried. The processed stripshowed good definition and speed.

In order to show that the cyclohexane compounds of ourlinvention areunique in photographic developers, one of the exposed strips wasprocessed in a manner identical to that illustrated in the aboveexample, except that the cyclohexane compound was omitted from the colordeveloper. The strip processed in the color developer containing thecyclohexane compound had a D-max. difference of only -.14 compared tothe control strip. On the other hand, when one of the exposed strips ofExample 1 was processed as described in that example, except thatcyclohexylamine was used in place of the 1,4-bis(methylamiho)cyclohexanein the color developer, there was a magenta D-max. difference of .48compared to the control. These results can be summarized as follows.

AD-max.

E Addenda-Color developer: from control I Control Cyclohexylamine .481,4-bis(methylamino)cyclohexane .14

7 Example 2 A multi-layer photographic element of the type described inMannes et al. US. Patent 2,252,718, issued August 19, 1941, was exposedto an original multi-colored scene and developed for about 3% minutes at80 F. in a developer having the following composition:

The photographic element was then spray washed with Water for about 30seconds and exposed to red illumination of about 1100 ft. candleseconds. The exposed material was then developed in a cyan developerhaving the following formula:

Water to one liter.

1 Sodium tetraphosphate.

'- As hydrochloride.

3 2-(o-acetamido-B-phenylethyl)-l-hydroxynaphthamidc.

The photographic element was then washed for about 30 seconds with waterand exposed to blue light of 300 ft. candle seconds intensity anddeveloped in a yellow colorproducing developer containing aphenylenediamine color developing agent, such as4-amino-N,N-diethylaniline hydrochloride and a yellow coupler, such asCoupler No. 47 from column 4 of US. Patent 2,956,876. The photographicelement was then washed and fogged chemically by treatment with a sodiumborohydride solution. The photographic element was then developed in amagenta color developer containing a color-developing agent, such asthat used in Example 1 above and a magenta coupler, such as Coupler No.30 in column 4 of U.S. Patent 2,956,876.

The photographic element was then bleached, fixed and dried as describedin Example 1.

As compared with a photographic element which had been similarlyprocessed using a negative developer containing 6.5 grams per liter ofisopropylamine. it was noted that there was a substantial speed increasefor the material processed in the 4-aminocyelohexanol (approximately /2stop), that there was a relatively small loss -in reversal D-max. (0.15unit) and that there was an increase in the speed/fog ratio compared tothe material processed in the developer containing the isopropylamine.In order to produce a material processed in a negative developercontaining isopropylamine and provide a speed comparable to materialprocessed in the 4-aminocyclo hexanol-containing developer, it was foundnecessary to increase the isopropylamine concentration to such an extentthat the D-max. of the resulting image was materially reduced in alllayers of the elements.

Example 3 Example 2 was repeated using a negative developer containing6.0 grams per liter of l-cyclohexylamino-Z- propanol in place of the4-aminoeyclohexanol used in Example 2. Again, there was a substantialincrease in speed compared to material processed in a negative developercontaining isopropylamine as the silver halide solvent.

The invention has been described in detail with particular reference topreferred embodiments thereof, but it will be understood that variationsand modifications can be effected within the spirit and scope of theinvention as described hereinabove and as defined in the appendedclaims.

What We claim as our invention and desire secured by Letters Patent ofthe United States is: I

1. A photographic developing composition consisting of an aqueousalkaline solution comprising a photographic developing agent and asilver halide solvent comprising a cyclohexane containing an aminoradical attached to the carbocyclic ring thereof and in addition tosaidamino radical, a polar substituent selected from the classconsisting of an amino radical, a hydroxyalkyl radical.

2. A photographic of an aqueous alkaline solution comprising aphotographic developing agent and 1,'4-bis(methylamino)cyclohexane.

3. A photographic developing composition consisting of an aqueousalkaline solution comprising a photographic developing agent and4-aminocyclohexanol.

4. A photographic developing composition consisting of an aqueousalkaline solution comprising, a photographic developing agent and1-cyclohexylamino-2=propanol.

5. A photographic developing composition consisting of an aquoeusalkaline solution comprising at least one photographic developing agentselected from the class consisting ofv 3-pyrazolidones, dihydroxybenzenes and p-N- hydroxyl radical and a a developing borhfioiiidiiconsisting" 12. A photographic developing composi on as defined'inplair'ir 11 wherein said aqueous alkaline solution con- I'halide-developingagentto produce a colored image.

methylaminophenol salts, and a'silver halide solvent com-- prising acyclohexane containing an amino radical attached to the carbocyclic ringthereof and in addition to said amino radical, a polarsubstituent'selected from the class consisting of an amino radical, ahydroxyl radical and a hydroxyalkyl radical.

6. A photographic developing composition consisting of an aqueousalkaline solution comprising at least one photographic silver halidedeveloping agent selected from the class consisting of 3-pyrazolidones,dihydroxybenzenes and p-N-methylaminophenol salts, and1,4-bis(methylamino)cyclohexane.

7. A photographic developing composition consisting of an aqueousalkaline solution comprising at least one photographic silver halidedeveloping agent selected from the class consisting of 3-pyrazolidones,dihydroxybenzenes and p-N-methylaminophenol salts, and4-aminocyclohexanol.

8.'A photographic developing composition consisting of an aqueousalkaline solution comprising at least one photographic silver halidedeveloping agent selected from the class consisting of 3-pyrazolidones,dihydroxybenzenes and p-N-methylaminophenol salts, andl-cyclohexylamino-2-propanol.

9. A photographic developing composition consisting of an aqueousalkaline solution comprising a phenylenediamine photographic silverhalide developing agent and a silver halide solvent comprising acyclohexane containing an amino radical attached to the carbocyclic ringthereof and in addition to said amino radical, a polar substituentselected from the class consisting of an amino radical, a hydroxylradical and a hydroxyalkyl radical.

10. A photographic developing composition as defined in claim 9 whereinsaid aqueous alkaline solution contains a color-forming compound capableof coupling with the oxidation products of said phenylenediamine silverhalide developing agent to produce a colored image.

11. A photographic developing composition consisting of an aqueousalkaline solution comprising a p-N-phenylenediamine photographic silverhalide developing agent and 1,4-bis(methylamino)cyclohexane.

15. A photographic developing composition consisting of an aqueousalkaline solution comprising a p-phenylenediamine photographic silverhalide developing agent and -1-cyclohexylamino-2-propanol. I

16. A photographic developing composition as defined in claim 15 whereinsaid aqueous alkaline solution contains a color-forming compoundcapableof couplingwith the oxidation products "ofsaid"p-phenylenediamine silverhalide developing agent to produce a colored image.

17. In the reversal process of color photography for producing a coloredimage in a photoexposed multilayer color material having sensitivity indiscrete areas thereof in the red, green and blue regions, respectifv Iof the visible spectrum, by first developing a black-andwhite negativeimage, followed by at least one development in a color developer toproduce a color record, the step of incorporating in at least one of thedeveloping,

compositions a silverhalide solvent comprising a cyclohexane containingan amino radical attached to the carbocyclic ring thereof and inaddition to said amino radical, a polar substituent selected from theclass consisting of an amino radical, a hydroxyl rad ical and ahydroxyalkyl I radical.

18. A process according to claim 17 wherein said sil 19. A processaccording to claim 17 wherein said silver halide solvent is4-aminocyelohexanol.

20. A process according to claim 17 wherein said silver halide solventis 1-cyclohexylamino-2-propanol.

References Cited in the file this patent UNITED STATES PATENTS 2,306,923Wood Dec. 29, 1942 2,857,276 Land et al. Oct. 21, 1958 3,004,850Dickinson et al. ...2 Oct. 17, 1961 FOREIGN PATENTS OTHER-REFERENCESGermany Ian. 5, 1955 UNITED STATES PATENT OFFICE CERTIFICATE OFCORRECTION Patent No. 3, 128,182 April 7, 1964 Charlton c. Bard et a1,

' It is hereby certified that error appears in the above numbered patent'req'liring correction and that the said Letters Patent should read ascorrected below.

Column 9, line 56, for "p-Nphenyl" read p-phenyl- Signed and sealed this4th day of August 1964.

' (SEAL) A ttestf ERNEST w. SWIDER EDWARD J. BRENNER Atmsting OfficerCommissioner of Patents

1. A PHOTOGRAPHIC DEVELOPING COMPOSITION CONSISTING OF AN AQUEOUSALKALINE SOLUTION COMPRISING A PHOTOGRAPHIC DEVELOPING AGENT AND ASILVER HALIDE SOLVENT COMPRISING A CYCLOHEXANE CONTAINING AN AMINORADICAL ATTACHED TO THE CARBOCYCLIC RING THEREOF AND IN ADDITION TO SAIDAMINO RADICAL, A POLAR SUBSTITUENT SELECTED FROM THE CLASS CONSISTING OFAN AMINO RADICAL, A HYDROXYL RADICAL AND A HYDROXYALKYL RADICAL.
 6. APHOTOGRAPHIC DEVELOPING COMPOSITION CONSISTING OF AN AQUEOUS ALKALINESOLUTION COMPRISING AT LEAST ONE PHOTOGRAPHIC SILVER HALIDE DEVELOPINGAGENT SELECTED FROM THE CLASS CONSISTING OF 3-PYRAZOLIDONES,DIHYDROXYBENZENES AND P-N-METHYLAMINOPHENOL SALTS, AND1,4-BIS(METHYLAMINO)-CYCLOHEXANE.